Studies on C20-diterpenoid alkaloids: synthesis of the hetidine framework and its application to the synthesis of dihydronavirine and the atisine skeleton.
J Org Chem
; 79(15): 6783-800, 2014 Aug 01.
Article
em En
| MEDLINE
| ID: mdl-25004408
ABSTRACT
The full details of a synthesis of the hetidine framework of the C20-diterpenoid alkaloids and its conversion to the atisine core structure are reported. The application of the hetidine framework to the synthesis of dihydronavirine, which is the formal reduction product of the natural product navirine, is also described. Key to the success of these studies is the use of a Ga(III)-catalyzed cycloisomerization reaction of alkynylindenes to prepare a [6-7-6] framework that was advanced to the hetidine skeleton. Furthermore, a Michael/aldol sequence was developed for the construction of the bicyclo[2.2.2] framework that is characteristic of the hetidines and atisines.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Produtos Biológicos
/
Diterpenos
/
Alcaloides
/
Alcinos
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2014
Tipo de documento:
Article
País de afiliação:
Estados Unidos